Stereoselective access to the versatile 4-aminohex-5-ene-1,2,3-triol pattern |
| |
Authors: | Ayad Tahar Faugeroux Vanessa Génisson Yves André Chantal Baltas Michel Gorrichon Liliane |
| |
Affiliation: | Laboratoire Synthèse et Physicochimie des Molécules d'Intéret Biologique, UMR 5068 CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 04, France. |
| |
Abstract: | We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH(4))(2)CO(3)-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|